


A Day on the Town

by sockablock



Category: Critical Role (Web Series)
Genre: Gen, Jester and Caleb's friendship!, Jester is a Menace to Store Clerks, Post Ep. 13, So much fluff holy shit all the fluff, friendship fic
Language: English
Status: Completed
Published: 2018-04-12
Updated: 2018-04-12
Packaged: 2019-04-22 02:53:35
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,199
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14299197
Author URL: https://archiveofourown.org/users/sockablock/pseuds/sockablock
Summary: Jester drags Caleb along for a day of hanging out in Zadash





	A Day on the Town

**Author's Note:**

> Thanks for reading! This is based off a prompt sent to me @sailorfjord on tumblr:
> 
> @transparentinternettragedy asked: I’d love some Caleb and Jester Friendship Fluff, after Episode 13 :)

“Caleb!” beamed Jester as she blasted through the wooden door. “Good morning! How are you doing?”

Nott was the first to react. Her head shot up from just behind the footboard, teeth bared and a crossbow bolt trained at the doorframe. There was a moment, where Jester continued to grin and waited for the little goblin’s sleep-heavy brain cells to catch up.

Eventually, Nott lowered the weapon sheepishly. “Sorry, Jester. Force of habit.” She gave a wide smile—which was no less terrifying than before—and said, “What brings you to our room so early?”

“Is Caleb awake?” Jester asked.

Both girls looked back at the large lump that had shoved its head under the pillows. 

“Caleb?” Nott prodded at his legs with the crossbow. “Jester’s here to see you.”

There was a string of muttered Zemnian, muffled by the pillow and by the annoyance. 

“Caleb, it’s time to wake up!” Jester announced. “We have a lot to do today, and not enough time for any of it!”

More Zemnian, but Jester could hear that his will was on the verge of breaking.

“Come on, Caleb! Wakey, wakey, doughnuts and pastries!”

He finally rolled onto his back and leveled a heavy glare at the door. “Jester, _why_ are you here?”

Jester seemed completely unaffected by the question. “You are my friend!” she said. “That means we have to spend time together. And since we’re done with all that crazy tower exploding stuff and Molly’s off figuring out his entire life with Fjord and Beau and Yasha in the criminal underground, I thought you and me could hang out!”

There was a moment, where Caleb tried to process this. 

“Nott, you could come too if you like?”

Nott, with her rather high intelligence, weighed the atmosphere. “If it’s all the same to you, I think I’d rather go out and try and get some more buttons today. Or sticks or something.”

As she spoke, Caleb’s expression had softened to the point where Jester could sense her complete and unyielding victory. 

“Alright, _ja_ , I’ll…hang out with you, Jester,” sighed Caleb, and sat up. Then his brow furrowed, and he gave Nott a faintly amused look. “Why do you have a crossbow?” he asked.

She shrugged, and the string made a whoosh sound as it went up and down. “In case someone came here looking after the dodeca-thingy,” she said.

Jester waltzed over the bed to give Nott a high-five. “Nott, you are so smart,” she said.

“I…yes, yes she is,” conceded Caleb. “Give me a couple minutes to get my stuff together, and I’ll meet you downstairs, Jester,” he sighed.

\---------------------

He was yanked through the door of the Leaky Tap before he could sit down at the bar for breakfast.

“Not here!” Jester announced cheerily. “We’re going to somewhere else!” 

Caleb gave another sigh. “If you say so.”

They tore through the Interstead Sprawl, Caleb trailing after the high-energy blue blur that paved the way for him. Frumpkin expertly wove between their legs in the effortlessly graceful manner of self-confident felines, and the jingling of Jester’s jewelry and various baubles was just barely audible over the din of the crowd. 

Despite the near-suffocating mass of bodies and the loud voices of merchants barking their wares and customers trying to haggle, it was almost soothing, in a weirdly overwhelming way. Nobody was paying Caleb any mind, and Jester’s steadily ringing metal decorations was giving Caleb something to focus on. She was wearing more than usual, he noticed, and was starting to wonder if she did that on—

“We’re here!” Jester stopped abruptly, and Caleb stumbled next to her. They were in the Pentamarket now, standing at the entrance of a little stone building, smoke coming out of the chimney and warmth leaking out the open door. 

“It’s a bakery,” said Jester. “I told you we were getting doughnuts and pastries.”

Caleb raised an eyebrow. “I never doubted that. After you, miss.”

She giggled at that, and walked in confidently. 

As Jester dumped the haversack onto the counter and started listing off the desserts she wanted—and the chocolate croissants, and the blueberry muffins, and I want those little apple things, no, those over there, and I want—Caleb watched a small child with frosting smeared on her face approach his cat with a small bit of pastry.

Frumpkin seemed to consider this offering for a moment, then deemed it acceptable and toughed it out as the child started patting down the fur on his back.

Jester swung around to face Caleb. “I’m finished!” she announced. “Here, this is for you,” and she handed him a loaf of bread.

He accepted it with mild surprise. “What? Oh… _danke_ , Jester. I’ll, um…should we get some forks or something?”

Jester snorted. “No, silly!” Then, as Caleb’s surprise grew, she produced another loaf and shoved her fists into the side. “You’re supposed to do it like this, right?” she asked.

He blinked a few times. “Uh…yes. But I thought you didn’t like it when I did that—”

“Don’t be silly!” Jester yelled, startling the child and everyone else in the bakery. “It’s a great idea, and now we’re going outside so put on your bread mittens and let’s go.”

She marched out the door. With a quick, confused glance at Frumpkin and an apologetic shrug at the rest of the patrons, he shoved his hands into the loaf and followed after her.

\---------------------

“Where to next?” Caleb asked.

Jester finished chewing, swallowed, and grinned at him. There were numerous bite marks in her bread loaf. “Bookstore!” she announced.

“Bookstore? But there aren’t any around here? Except the Archive, but it’s more of a library and besides, you need special access.”

“Well, ok,” Jester conceded, “it’s not actually a bookstore. It’s more of a pawn shop. I made Claudia tell me where it was before she left yesterday. Apparently, it’s called the Queen’s Pawn and there’s a big section of books.”

Caleb’s face lit up. “ _Where?_ ”

\---------------------

“Mein Gott, this is a copy of the critiques made on Mordenkainen’s Theory of Conjuration on the Material Plane! Oh, and it has the original footnotes and citations! Jester, this is wonderful!” Caleb whispered.

They were standing in the corner of the store, tucked away by the bookshelves and out of sight of the shop-owner, an older half-elf who had gone to the back for a lie-down after a dirty ginger and an exuberant blue tiefling had barged into his store with their hands in loaves of bread (half-eaten, in Jester’s case). 

“I’m very happy for you, Caleb,” Jester said. “Let me know if you find a copy of _Tusk Love,_ ok? Molly gave it to Dolan and I want another one.”

“Oh, and here is a dissertation on the arcane interactions of illusory enchantments on common metals!”

“Any spells?” Jester asked. “Uh…transmutant or evoking or anything?”

Caleb was too distracted to correct her. “No, but this is almost better! With these I can further my own studies, and work on developing…well, developing a lot of different things.”

“Oooh, that’s pretty cool,” said Jester supportively.

“You should look around for something too—”

Caleb turned around. Jester had rearranged every book on the shelves behind her so that the covers were in rainbow-order, and not at all in alphabetical order. Now she was sitting on top of a shelf and munching on a cinnamon roll. 

“I-I think I’m done browsing now. Would you like to come down and come with me to the checkout?”

She hopped down. “Lead the way…mister,” she said.

The owner was roused and the books presented.

“Oh, yes!” said the shopkeeper. “Yes, a young wizard came by a while ago and dropped them off. He needed the tuition money for the academy, as I understand.”

Jester leaned onto the counter. “So we should get a discount, then? Since these books are secondhand, and all.”

The shopkeeper gave her a look that many had given the Mighty Nein in the past. “This is a pawn shop, miss. Everything here is secondhand.”

Caleb put a hand on Jester’s shoulder, in a universal _please-don’t-say-anything-else-I-got-this_ gesture. “What my friend means,” he said, “is that we are delighted to uncover such a find in your fine establishment, and would be happy to pay any reasonable price for these books.”

\---------------------

“I had that,” Jester said without any resentment as they left the shop, “he was this close to giving them to us for free.”

“Why don’t you get that bread out from the bag, Jester? I’m still a bit hungry.”

“Oh, I will! But let’s wait until we get to the next place, ok? We can sit at a bench and keep eating. And it’ll give me somewhere to sort through all the books I stole from that man.”

\---------------------

“This is…rather pleasant, Jester.”

They were sitting at a bench in an open square back in the Interstead Sprawl. After spending so long sorting through the books in the pawn shop, and with the time they spent walking around, it was starting to creep past mid-afternoon. There were less people milling about now, with only a few individuals and the ever-present smattering of crownsguard. Jester had the haversack plopped next to her, and Frumpkin was seated her lap.

“Thank you,” she said cheerily. 

“Um…what are we going to do now?” he asked. 

She gave him a smile. “We’re going to sit here and you’re going to read, silly!” she said.

Caleb raised an eyebrow. “You’re just going to sit there while I’m reading?” he asked.

“No, don’t be dumb, I’m going to draw!” And she reached into the sack and pulled out her sketchbook and a piece of charcoal and got busy.

Caleb watched her hands move. She seemed completely absorbed in her work, and so after a few moments, he cracked open the critique and started to read.

At some point, mid-afternoon turned into late, late afternoon, with the sun just about to set. Caleb had already read the tome through twice, and was about to go back to see what he missed when a thought pushed through the book-crazed fog and into the front of his mind.

He turned to Jester, who was sketching a couple making out by the building across from them.

“Jester?” he asked.

She looked up. “Yes?”

“Uh…don’t take this the wrong way, alright? But I was just sort of wondering…why are you doing this? I know you said before that whole thing about the friends thing, but that can’t be _it_.”

She frowned. “What do you mean? Why can that not be it?”

He floundered for the right words. “Well…we are very different people. And all that stuff you did today, all of that was stuff that I like to do. I like putting my hands in bread and shopping for books and reading quietly.”

Jester gave him a look, and then started to laugh. When she got her breath back, she said, “Of course it is! Of course you like that stuff, of course! But you know what I like?”

He paused, trying to think of the right answer, but Jester broke his silence.

“I like getting pastries. And I like walking into weird little stores and looking at all the shiny things and changing the order of the books on the shelves. I like making little kids laugh when we bring Frumpkin places and I like confusing the heck out of store clerks. But there’s something else I like more than all those things.”

“Oh?”

She met his gaze, and for a moment the ever-present energy turned into a serene calm. “I like spending time with you, silly.” 

“Oh.”

“And, you know, you are my friend. And you’ve just been so sad lately, Caleb. So I thought I would help to cheer you up!”

Caleb wasn’t quite sure how to respond. But, as Jester patted him on the knee and turned back to her sketch, in the peaceful silence he realized that he didn’t really have to. 

Still, “Thank you, Jester,” he said.

She didn’t look up from her drawing, but he could see the grin on her face. “You’re welcome.”

Then Caleb steeled himself and said, “You know, maybe we should go do something else that you really like, though.”

“Oh? Like what?”

He took a deep breath. “Maybe…we could go to a bathhouse? And find a tailor or something so you can get yourself a new dress.”

She was on her feet in an instant. Frumpkin yowled as he was tossed out of her lap.  
“Really?! Really do you really mean that?!”

A faint smile flickered across Caleb’s face, and this time his sigh was less defeated and much more fond.

“I’ll even let you braid my hair after I wash it,” he said.

“Oh, yes! Yes, let’s go!”

She gave Caleb exactly six seconds to collect his things before she grabbed him by the wrist and took off through the city again, Frumpkin chasing their heels. 

“Will you _really_ let me braid your hair?” Jester shouted as they ran.

“Yes!” Caleb said, slightly out of breath. “I will!”

And he did.

**Author's Note:**

> If you want to send me a prompt too, do it! I'm @sailorfjord and while my other stuff is in the works, I'd love to fill some requests <3


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